Top 17 Best Leonardo DiCaprio Movies Of All Time

Leonardo DiCaprio has proven himself as one of the best actors in Hollywood. (If not THE best.) The way he can embody any character and bring them to life is, simply stated, impressive. Even though he shockingly only has one Oscar win under his belt, everyone in the history of the world pretty much knows he deserves more than that.

Leo first gained mainstream attention after a guest-starring arc on the ’80s sitcom Growing Pains. He can also be spotted in early ’90s TV shows like Roseanne and Parenthood. As we Leo fans all know, the actor soon made the switch from TV to movies and has been working strictly on the big screen ever since. The 43-year-old actor has somehow avoided scandal, become the poster boy for environmental activism, and stays out of the spotlight as much as he can. Oh yeah, and he’s super hot — duh. All of this is not new information to the true Leonardo DiCaprio fan, but if you think that title is yours — then you better have seen these 17 movies…

17. This Boy’s Life (1993)

In his first (major) film role, Leonardo DiCaprio was hand picked by Hollywood legend Robert DeNiro to play the role of author Tobias Wolff as a young teen. The movie is based on an autobiography of the author’s life and Leo portrayed an abused young boy in the 1950s. This movie role is seen as DiCaprio’s breakthrough performance and part of the reason he continued to snag major film roles in the future.

16. What’s Eating Gilbert Grape (1993)

Leonardo played Arnie Grape, a mentally disabled boy in this drama that’s also starring Johnny Depp as his older brother. Johnny’s character is tasked with not only keeping an eye on Arnie but caring for their morbidly obese mother. The movie is a tearjerker for sure, but the story behind it is so moving that it’s a must-see. Somehow there’s also a bit of humor carefully woven throughout. Leo’s performance was praised by critics and he was nominated for an Academy Award for the first time, but as we all know it would be a while before he was finally granted the honor…

15. The Basketball Diaries (1995)

I’m sorry, but look at this young Leonardo DiCaprio! He looks adorable! The Basketball Diaries is a coming of age drama depicting teen boys spiraling into drug addiction. DiCaprio’s charcater, Jim Carroll, wrote a book of the same name that inspired the movie. Soon, Jim’s drug addiction got out of control and he was forced into dealing with some serious consequences. DiCaprio was able to sensitively portray a young man dealing with addiction and even though he was only 21 when this flick came out, he proved himself to be one of the greats.

14. Romeo + Juliet (1996)

This modern(ish) take on the classic Shakespeare play gave us Leonardo Dicaprio as Romeo and Claire Danes as Juliet. This movie is best remembered for its stylized take on the iconic play and, of course, it’s soundtrack. It was through this mid-’90s film that Leo started his climb to heartthrob status, which would of course be peaked by another another classic on this list. It’s funny we were so taken with him and his character because rumor has it, Claire Dane’s was not his biggest fan on set because she found him to be super immature.

13. Titanic (1997)

And, well — duh! Here we are with the movie that solidified Leonardo DiCaprio as one of the most talented (and sexiest) actors of the ’90s. What a movie. A different take on star-crossed lovers and an ill-fated ending. We were all watching in suspense even though the story is historic. That’s how swept away we were by Leonardo DiCaprio and Kate Winslet‘s portrayal of Jack and Rose. We all know what happens in the end and the debate on whether or not they could’ve both fit on that door in the Atlantic forever lives on. This movie catapulted Leonard DiCaprio to stardom and his life hasn’t been the same since. TBH, neither has ours!

12. The Beach (2000)

Leo spends a good chunk of time of this movie shirtless, which, quite frankly, is a decent portion of the reason it’s on this list. But the real reason why every Leo fan needs to see it is that it actually might be his worst film. While it was financially successful, the movie was bashed by critics and has a dismal 19% rating on Rotten Tomatoes. The Beach was also pretty controversial when it came out. This is because they pretty heavily damaged an island in Thailand where they filmed to make it seem more “paradise-like” and Thai politicians were upst about the drug culture of Thailand that was depicted in the film.

11. Catch Me If You Can (2002)

Okay, we’re back to Leo’s very many GOOD movies. Though a crime drama, this movie has a lot of flair. It follows an early ’00s Leonardo Dicaprio playing Frank Abagnale Jr., a con artist posing as a pilot who launders millions of dollars… oh, and it’s a true story!

Tom Hanks portrays the frustrated detective trying to catch him and Leo’s the type of main character you can’t help but love. Catch Me If You Can really comes off more like a comedy while doing a fairly accurate portrayal of real-life characters dealing with some very real issues. It was even turned into a musical. Another Leo winner!

10. The Aviator (2004)

The Aviator is sweeping biographical drama in which Leonardo DiCaprio stars as filmmaker, businessman, and billionaire Howard Hughes. This film was a critical and commercial hit and was praised for both its attention to detail in the time period and accuracies surrounding Hughes’s life. We’ve got another good one showing Dicaprio’s range as he began the film as an eccentric billionaire and as it came to close embodied Hughes descent into mental illness as he ultimately became a recluse. This marked the second collaboration between Leonardo DiCaprio and Martin Scorsese and garned DiCaprio’s second Oscar nomination.

9. The Departed (2006)

This movie is a trip and a half. The second you think you know what’s happening, everything gets switched up. A film depicting the Irish mob in Boston, the deep connections of crime, the loyalty of mob members, and the utter danger of crime life, Leonard DiCaprio plays a police agent who goes undercover into a crime ring. Matt Damon also stars as a police officer who’s been trained as a mole for the mafia. Identities are revealed, webs of lies are woven, and no one seems to know wtf is happening. The audience included. This is another Martin Scorsese collab and the twists make this a crime drama one that can be watched over and over again (and one of Leo’s best films!).

8. Blood Diamond (2006)

This political drama is really an eye-opener. The film takes place during the Sierra Leon Civil War (1991-2002) and depicts a country being torn apart in the fight for diamonds mined and sold. Everyone is trying to get their hands on these rare diamonds, especially Leonard DiCaprio’s character, Danny Archer. What follows is a dangerous pursuit for a rare pink diamond and DiCaprio’s third Academy Award nomination.

7. Revolutionary Road (2008)

Reuniting with his Titanic co-star and real-life BFF, Kate Winslet and Leonardo DiCaprio portray an unhappily married couple, April and Frank Wheeler in the 1950s. After settling down in a suburban home and having children, April is bored of their life and convinces Frank to move to Paris for a change. But April falls pregnant again and plans change. This movie is so tragic, but the chemistry between Leo and Kate makes the whole thing so worth it.

6. Shutter Island (2010)

This psychological thriller is another Scorsese/DiCaprio collaboration and it’s perfectly unpredictable. The only thing on Shutter Island is a mental hospital for the criminally insane. DiCaprio plays U.S. Marshall Teddy Daniels, sent to Shutter Island to investigate the disappearance of a dangerous patient. The patient is incarcerated for drowning her three children and there’s seriously no way to predict what’s going to happen next. I won’t spoil this nearly eight-year-old movie (how have you not seen it yet?! You call yourself a Leo fan!) but it’s a total mind f*ck and obviously, another great performance from DiCaprio.

5. Inception (2010)

Speaking of mind f*cks, we bring to you Inception. Leonardo DiCaprio’s character is a thief working in corporate espionage to steal informaton by actually entering people’s subconscious. The only problem is if you can move in and out of someone else’s minds, how can anyone tell what is real and what is fiction? This movie was infamously confusing yet so cleverly done. If you haven’t seen it yet (and, again, do you even like Leonardo DiCaprio if you haven’t?!), do it now!

4. Django Unchained (2012)

In one of his darkest roles, Leonardo DiCaprio portrays slave owner Calvin J. Candie in this Quentin Tarantino film. A classicly violent Tarantino film, Calvin is a cruel slave owner who forces his slaves fight to the death for his own entertainment. While obviously we have no choice but to hate Leo’s guts in this film, the role is undeniably different from anything he’d ever done before. In interviews, DiCaprio described how he was disturbed and uncomfortable at some of the language he was required to use in the role as a racist and disgusting slave owner.

3. The Wolf of Wall Street (2013)

This inside look at Wall Street and the shenanigans that went on the 1980s is both hilarious and disturbing. These guys were such A-holes doing all kinds of illegal sh*t just to make more money. Leonardo DiCaprio plays grade-A douchebag Jordan Belfort (based on his real-life story) and we follow his rise and inevitable fall. It’s fun seeing DiCaprio in this role because he is usually somewhat reserved, in film and real life, and here he is way over the top. He also earned another Academy Award nomination for this role. Yet again, he was robbed of the win.

2. The Great Gatsby (2013)

This 2013 movie is another adaptation of the book we all read (or were supposed to read) in high school. Leonardo DiCaprio is Jay Gatsby, the mysterious millionaire who like to party. It’s a story of affairs, betrayals, murder, and heartache. This adaptation is very artistic and stylized, but stays fairly true to the F. Scott Fitzgerald classic novel. DiCaprio’s Gatsby is charming yet vulnerable and even though you know the ending, you’ll be rooting for him.

1. The Revenant (2016)

Proving that Leonardo DiCaprio loves to portray real people, here he is as frontiersman Hugh Glass. He gives a stirring performance of survival against a cruel wilderness, cruel people, and he also fights a huge bear. Surely you’ve heard of that epic battle by now. DiCaprio completely carries this movie and *finally* won the elusive Academy Award for Best Actor after five nominations! There was a whole campiagn for his win because he truly deserved it.

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